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Thomaston Holiday Rentals

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Holiday Rentals in Thomaston

136 Raymond · Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (20)
"Immaculate Victorian home wonderfully renovated for modern convenience. Perfect Location; easy on/off Interstate 84. Gracious host who was ultra responsive. Very pleasant stay. "
136 Raymond · Prime West Hartford Center Location: Historic Gem

Beautiful cozy rooms near hospital and down town area

8.0 out of 10, Very good, (17)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
The price is AU$390
includes taxes & fees
28 Nov - 29 Nov
Beautiful cozy rooms near hospital and down town area

Spectacular Short Term Vacation Rental in Kent

9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent

Newly renovated cottage on the lake!

10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!

Peaceful apartment on 3.5 acres w/ artist studio.

9.8 out of 10, Exceptional, (14)
"We were only here for one night on a whirlwind trip but would gladly have stayed a little longer. Cozy, woodsy and comfy. Nice place to relax and recharge! We really appreciated the excellent (real) coffee! No pods here :) Saleem was great - very helpful!"
The price is AU$329
includes taxes & fees
9 Dec - 10 Dec
Peaceful apartment on 3.5 acres w/ artist studio.

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is AU$180
includes taxes & fees
28 Nov - 29 Nov
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (65)
"This property is a remodeled older house. With all that old house charm. It is spacious and has three bedrooms, each with a queen bed. The couch is extremely comfortable and it was great watching TV and sipping wine."
Fun Downtown Location 2nd flr

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (19)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

lakefront estate

3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate

Candlewood Lake Retreat with year round views

10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views

The Long View of Candlewood Lake

10.0 out of 10, Exceptional, (17)
"The house faces the lake and offers tranquil and beautiful views from most rooms. It was meticulously maintained and very attractive and comfortable. It was stocked with everything you would need to be comfortable and to feel like home. We stayed 2 nights and thoroughly enjoyed it!"
The Long View of Candlewood Lake

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
River Overlook - Check the view from your deck!

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade

NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

10.0 out of 10, Exceptional, (3)
"First time booking and the place was perfect, beautiful views, real cozy vibes, and the host did a great job to attend at anything we needed "
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*

10.0 out of 10, Exceptional, (2)
"The upstairs kitchen may need some extra ceramic bowls and silverware. The hot water may need to be turned up, it was tepid at best. Jeff was more than helpful getting us situated and comfortable. Great neighborhood, and availability to groceries, restaurants, and the great brewery 2 minutes away. Great room for families for togetherness and privacy"
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (16)
"I had an absolutely wonderful weekend. The home was clean, cozy, and exactly as described in the listing. From the moment I arrived, I felt right at home. Mariana was incredibly responsive and helpful and ensuring I had everything I needed throughout my stay. I will be coming back again."
Cozy & Chic Cabin by the Lake, with access to private Beach!

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (40)
"Beautiful cottage, spectacular property, wonderful hosts. Not sure what else to say? We came up to CT with our pup to look at areas we may want to move to. The cottage was perfect for us, nice and private and lots of land for our pup to walk. Great state park a few miles away and plenty of good restaurants nearby. Very happy!"
Guest Cottage on Country Estate

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

9.6 out of 10, Exceptional, (4)
"This property appeared to be recently built. While the neighborhood is nice and appeared to be safe, there were not enough utensils for the 6 people in our party. I also requested the check-in code at least the night before we arrived and that did not happen. As of the morning we flew out to Hartford, I hadn't received the check in code...very frustrating. Also the only chairs to sit in were in the downstairs living room and kitchen. If you wanted to watch TV in a bedroom, your only option was...
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Thomaston you may be interested in

Holiday Inn Express Southington, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (1169)
"The hotel was nice. Stuart at check in was very helpful and friendly. Good breakfast options. Can’t beat the hot and gooey cinnamon rolls. Comfy bed and good location. We would stay again. "
The price is AU$205
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Southington, an IHG Hotel

Red Roof Inn Meriden

2.0 star property
7.6 out of 10, Good, (1086)
"Room was ok clean, but needs some work. Is outdated. "
The price is AU$156
includes taxes & fees
28 Nov - 29 Nov
Red Roof Inn Meriden

Courtyard by Marriott Waterbury Downtown

3.0 star property
8.4 out of 10, Very good, (1102)
"I would stay there again"
The price is AU$149
includes taxes & fees
1 Dec - 2 Dec
Courtyard by Marriott Waterbury Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Thomaston?

Yes, there are holiday rentals close to the most popular sights in Thomaston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Thomaston has to offer?

Spectacular Short Term Vacation Rental in Kent: This holiday home rental outside of Thomaston is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Thomaston?

Explore the area and family-friendly sights such as The Christmas Shop, or get out into nature at a spot like Black Rock State Park. In the wider area, you’ll find Haight-Brown Vineyard and Litchfield Town Green.

What’s a holiday rental in Thomaston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Thomaston. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips.